Category: Triazoles

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, A new synthetic method of this compound is introduced below., name: 5-Methyl-4H-1,2,4-triazol-3-amine

General procedure: 3-Amino-1,2,4-triazole 8a-f (1.0 mmol), o-hydroxybenzaldehyde9a-e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3¡Á1 ml), and dried. Compounds 1a-w were obtainedin a form of white solids.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Guemue?, Mustafa K.; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Chebanov, Valentin A.; Desenko, Sergey M.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1261 – 1267; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1261 – 1267,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 15988-11-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: General procedure: A mixture of 4-phenylurazole (1, 1 mmol), aryl aldehyde (2, 1.1 mmol) or ketone (5, 1.1 mmol), 1,3-diketone (3, 1 mmol) and FeCl3 (16.2 mg, 10 mol%) in acetonitrile (2.5 mL) was stirred in preheated oil bath at reflux for a specified time as required to complete the reaction (see Table 2 and 3). After complete conversion, as indicated by TLC, the solvent was removed in vacuo and the residue was diluted with water and extracted with ethyl acetate (2¡Á10 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (Merck, 60-120 mesh, ethyl acetate:hexane, 4:6) to afford the pure triazolo[1,2-a]indazoletrione or spirotriazolo[1,2-a]indazoletetraonederivative.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Phenyl-1,2,4-triazolidine-3,5-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Subba Reddy; Umadevi; Narasimhulu; Yadav; Chemistry Letters; vol. 42; 8; (2013); p. 927 – 929;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1533519-85-5, These common heterocyclic compound, 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Take 8.0g of the purified product of compound (4) obtained in Example 3, 64ml of tetrahydrofuran, start stirring, warm up to T=30~35C, stir until dissolved; add 6.4g NBS, stir the reaction for 3~4h, the reaction is completed, and the temperature is reduced to T 05, add 40ml of toluene, add 40ml of purified water dropwise, the temperature is controlled not to exceed 7, drop it, stir for 10min, let stand for liquid separation; the organic phase is cooled to 05, add 3% hydrogen sulfite dropwise 40ml of sodium solution, keep the temperature below 10C, drop after completion, stir for 20min, stand for liquid separation, collect organic phase; warm to 1825C with camera, add 40ml of 7% sodium bicarbonate solution, stir for 10min, stand for liquid separation , Collect the organic phase, concentrate and dry to prepare the Recinade product, and test its purity to 99.940%.

Statistics shows that Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate is playing an increasingly important role. we look forward to future research findings about 1533519-85-5.

Reference:
Patent; Beijing Xinkaiyuan Pharmaceutical Technology Co., Ltd. Hainan Fen Corporation; Xia Zhongning; Wu Jin; Wang Shiwei; (10 pag.)CN111116500; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

815588-93-3, name is 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: Triazoles

[00152] To a stirring solution of 7 (0.315 g, 2.48 mmol) in CH2C12 (60 mL) was added EDCI.HC1 (336 mg, 1.76 mmol), HOBt (297 mg, 2.20 mmol), DIPEA (0.67 mL, 3.67 mmol) and Int-C (0.5 g, 1.47 mmol) at 0¡ãC. The reaction mixture was stirred at RT for 16 h. After consumption of the starting material (by TLC), the reaction mixture was diluted with DCM and washed with water. The separated organic layer was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to obtain crude product. This material was purified bycolumn chromatography followed by prep-HPLC purification to afford Compound D (80 mg, 12percent). H-NMR: (400 MHz, DMSO-d6): delta 8.09 (s, 1H), 4.55-4.51 (m, 1H), 4.08 (d, 2H), 3.97 (s, 2H), 3.87-3.84 (m, 3H), 3.70-3.55 (m, 2H), 3.45 (t, 1H), 3.35-3.31 (m, 2H), 2.75 (s, 3H), 2.27-2.24 (m, 2H), 1.98-1.92 (m, 4H), 1.85-1.84 (m, 2H), 1.19 (d, 3H). LCMS (m/z): 448 [M++l]

The synthetic route of 815588-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAUREX, INC.; LOWE, John, A.; KHAN, M., Amin; WO2014/120800; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1455-77-2,Some common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A suspension of 3,5-diamino-1,2,4-triazole (0.1 g, 1 mmol) in absolute EtOH (10 mL) was added to a stirring solution of azo-coupled precursors, Ia-IVa, (2 mmol) in absolute EtOH (50 mL) during a period of 10 min at 60-70 ¡ãC. The mixture was heated in water bath for 15 h at 80 ¡ãC with stirring. The mixture was filtered whilst hot and the obtained solid was washed with hot ethanol (three time) and then with diethylether. The resulted product was dried in air.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Diamino-1,2,4-triazole, its application will become more common.

Reference:
Article; Khanmohammadi, Hamid; Erfantalab, Malihe; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 86; (2012); p. 39 – 43;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 956317-36-5,Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-2, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to 00C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-4 as a yellow solid.

The synthetic route of 956317-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FLORES, Broc; SCHREIER, John, D.; WO2010/48016; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

lH-l,2,3-triazole-4-carboxylic acid (15.9 mg, 141 muiotaetaomicron) and HATU (53.5 mg, 141 muiotaetaomicron) were dissolved in DMF (2 mL) and stirred for 15 minutes at room temperature. (2R,^R)-4-Amino-2-azido-5-(5′-chloro-2′-fluorobiphenyl-4-yl)pentanoic acid ethyl ester (50 mg, 128 muiotaetaomicron) and DIPEA (67 mu^, 384 muiotaetaomicron) were added, and the mixture was stirred at room temperature for 15 minutes then concentrated in vacuo and the residue was dissolved in EtOH (2 mL). An aqueous solution of IN NaOH (1.3 mL, 1.3 mmol) was added, and the mixture was stirred at room temperature for 30 minutes then concentrated in vacuo and the residue was purified by reverse phase chromatography to yield Compound 1 (45 mg).

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 15294-81-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 15294-81-2 as follows.

A mixture of 4,5-dibromo-1,2,3-triazole (1.0 mmol, 227 mg) and Na2SO3 (3.0 mmol, 378 mg) in water (3.0 mL) was stirred at 100 C (hot plate) for 3 days. The mixture was cooled to rt, then extracted with ethyl acetate (5 mL x 2). The combined extract was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was crystallized from ethyl acetate and heptane to give the desired product as a white solid (99 mg, 67% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.10 (s, 1H) ppm. 13C NMR (100 MHz, DMSO-d6) delta 130.6, 120.5 ppm. HRMS calculated for [C2H2BrN3+H]+ 147.9505, found: 147.9502.

According to the analysis of related databases, 15294-81-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sakurada, Isao; Tetrahedron Letters; vol. 58; 32; (2017); p. 3188 – 3190;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 151899-62-6, name is 3-Iodo-1-trityl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Iodo-1-trityl-1H-1,2,4-triazole

Step 2: Preparation of 5-(3-chloro-4-fluorophenyl)-3-methyl-3-(pyrimidin-5-ylmethyl)-l-(l- trityl-l,2,4-triazol-3yl)-l,3-dihydro-2H-indol-2-oneTo 5-(3-chloro-4-fluorophenyl)-3-methyl- 1 -pyrimidin-2-yl- 1 ,3-dihydro-2H-indol-2-one (648 mg, 1.76 mmol), l-trityl-3-iodo-l,2,4-triazole (809 mg, 1.85 mmol, prepared using similar procedures as described in US Pat. No. 5,393,732 incorporated herein by reference in its entirety. Potassium carbonate (1071 mg, 7.75 mmol), N, N’-dimethylethylenediamine (0.300 mL, 2.82 mmol) and copper (I) iodide (268 mg, 1.41 mmol) under nitrogen was added toluene (15 mL).The mixture was stirred at 100 0C for 18 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with 0-100% ethyl acetate/hexanes, to afford -(3-chloro-4- fluorophenyl)-3-methyl-l-pyrimidin-2-yl-l,3-dihydro-2H-indol-2-one as a white solid. 1H NMR (CDCl3): delta 8.98 (s, 1 H), 8.34 (s, 2 H), 8.04 (s, 1 H), 7.56 (m, 1 H), 7.41 (m, 1 H), 7.30(m, 18 H), 7.05 (d, 1 H, J = 8.3 Hz), 3.31 (d, I H1 J = 13.7 Hz), 3.12 (d, I H1 J = 13.8 Hz) 1.59 (s,3H)MS: m/e 699.24 (M + Na)+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 151899-62-6.

Reference:
Patent; MERCK & CO., INC.; WO2009/45386; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 74205-82-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74205-82-6 name is (1H-1,2,4-Triazol-1-yl)methanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture containing 25 ml of acetonitrile, two equivalents of (3,5-dimethyl-1H-pyrazol-1-yl) methanol (compound 2), and one equivalent of N,N-Diethyl-propanediamine was stirred at room temperature for 4 days. Next, the solvent was concentrated at a reduced pressure, washed with brine and dichloromethane. The organic solution was dried with MgSO4, and the solvent was concentrated at reduced pressure to yield compound 3 as light yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-1,2,4-Triazol-1-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Bendaha, Hasnae; Yu, Lisa; Touzani, Rachid; Souane, Rachid; Giaever, Guri; Nislow, Corey; Boone, Charles; El Kadiri, Sghir; Brown, Grant W.; Bellaoui, Mohammed; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4117 – 4124;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics